Diastereoselective construction of structurally diverse 2,3-dihydroquinolin-4-one scaffolds via redox neutral cascade [1,7]-hydride transfer/cyclization

Literature Information

Publication Date 2021-12-07
DOI 10.1039/D1QO01530C
Impact Factor 5.281
Authors

Ronghao Xie, Shixiao Chen, Xianping Xiang, Xiangcong Yin, Lubin Xu, Shuai-Shuai Li, Liang Wang, Fengying Dong


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Abstract

The pharmaceutically significant 2,3-dihydroquinolin-4-one scaffolds were constructed diastereoselectively and facilely via redox-neutral cascade Knoevengel condensation/[1,7]-hydride transfer/cyclization/transesterification in DCE from readily available methyl 2-aminobenzoacetate and diverse aldehydes, which features novel and highly valuable product structures, diastereoselective construction of all-carbon quaternary centers carrying allylic or propargyl groups as well as a privileged 3-spirocyclic 3,4-dihydrocoumarin moiety, an unusual pattern of [1,7]-hydride transfer, broad substrate scope, etc.

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Organic Chemistry Frontiers
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Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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